‘We are in it for the long term’

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Jonathan Stephenson on Brit Bermuda’s buildout

Taking a measured RISK KICK-STARTED Jonathan Stephenson’s career in reinsurance. Having studied math and physics at university, he quickly realized that the scientific field wasn’t the right one for him. Stephenson did, however, have a curiosity around the language of numbers. “I went into finance and studied math [as it] applied to money,” he told IB. “Coming out of an undergraduate degree a little bit older than my fellow graduating students – who all wanted to be investment bankers and stockbrokers and bond traders – I thought I wanted to do something a little bit different.” After discovering reinsurance in a risk management course in applied corporate finance, Stephenson quickly became hooked, looking at math and numbers as they applied to risk. Intrigued by the scale of capital moving through reinsurance markets, he made up his mind.

Brit Re is the Bermuda-based reinsurance platform of Brit Ltd. Brit Re was incorporated in 2007 and holds a Class 4 license issued by the Bermuda Monetary Authority to underwrite (re)insurance business. Brit Re provides reinsurance solutions for clients based in the US, Bermuda and globally, underwriting a diversified portfolio of property, casualty and specialty business.

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“The brokers have been very, very responsive to our arrival. We’ve been very fortunate to establish a great deal of new relationships and build on existing ones ”

Jonathan Stephenson, Brit Re

“I came out of university with the desire to pursue a reinsurance career. [However], I was in Montreal and there isn’t a huge industry in Montreal from a reinsurance perspective. So, I found my way to Toronto and pounded the streets, knocking on doors, trying to find my way into the reinsurance business. Ultimately, I was fortunate enough to be hired by Guy Carpenter in 1991.” Building out a Bermuda-led third-party reinsurance businessStephenson’s early years at Guy Carpenter gave him a solid foundation – one that would support a global career. “I’ve spent my time in Toronto, a little bit of time in London, some in New York, went and ran their operations in Sydney, Australia, came back to Canada – spent a few years working at Aon, then returned to Guy Carpenter.”

Published 15 Dec 2025

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“I can say that we’ve met those plans or exceeded them from a property and casualty and cyber perspective. [And], of course, we’re very pleased with that outcome”

Jonathan Stephenson, Brit Re

In all that time, however, and through all that change, one relationship remained constant. “Interestingly, for all of my broking career and in whichever shop I worked at, I always had some exposure to the Fairfax companies as clients and, of course, as markets. I’ve known the business quite well for the entirety of my career. So, the opportunity to be a part of it was too good.” In 2024, that job became official when Stephenson was appointed to lead the buildout of Brit Re in Bermuda.

“Brit has actually been on the island since 2017,” added Stephenson. “Our principal business was reinsuring our own book of insurance emanating from our Lloyd’s Syndicate in London. With the buildout of Brit Re we announced last year, we felt that there was an opportunity to leverage the great brand that had been established over the 30-year history of Brit, to leverage the balance sheet that had been established here in Bermuda and, with the backing of Fairfax, build out a third-party reinsurance business here in the Bermuda market.” Importantly, the firm wasn’t looking to replicate what others were doing. Brit’s product offering is geared to differentiating them in the market, taking advantage of their rating, their balance sheet and the backing of the firm. “[It’s about] responding to the demand that we saw among clients for additional Bermuda capacity – [and] that’s capacity across different product lines. Rather than an entry into just property cat, which we had been writing already, we wanted to combine that with cyber and casualty underwriting to create a multi-line product offering to help differentiate us on the island.”

‘A statement about Brit Re’s intent’ And the response from the market has affirmed the success of the strategy, with Stephenson characterizing it as more than proving the investment thesis. In keeping with this confident launch, Brit Re jump-started its renewed presence with a bold statement – hosting its launch at the Masterworks Museum of Bermudian Art. “That wasn’t just because it’s an interesting venue but also because it was a statement about Brit Re’s intent to establish ourselves as a long-term participant in the market here in Bermuda,” explained Stephenson. A year later, the tone remains shiningly optimistic. As Stephenson told IB, the reception has been fantastic. “The brokers have been very, very responsive to our arrival.

We’ve been very fortunate to establish a great deal of new relationships and build on existing ones with a good cross-section of high-quality insurance enterprises.” And while Brit Re came into the year with ambitious plans, Stephenson is quick to point out that they more than delivered this. “I can say that we’ve met those plans or exceeded them from a property and casualty and cyber perspective. [And], of course, we’re very pleased with that outcome. We’ve also tried to be quite visible this year. We’ve made sure that we’ve attended CIAB, APCIA and Baden-Baden most recently. With each of those events, we’ve been afforded the opportunity not just to spend time with insurance company executives and the brokers that support them, but also with industry peers, finding our way gently into the marketplace. The reception has been very, very good. We’re confident that there’s more appetite in the reinsurance market for Brit Re.”

Expanding beyond ‘business-as-usual’As the firm looks toward 2026, Brit Re’s priority is smart – aligned growth and building on the success of the past year. “Our focus for the year has been close to the historical appetites of Brit’s existing reinsurance franchise,” Stephenson added. “That has been, although not exclusively, about North American property catastrophe business and the support of proportional casualty business emanating from the US.” This focus, he told IB, served a dual purpose – to build relationships and to ensure internal operations were battle-ready.

“It allows us to not just focus on the underwriting and the results that we were trying to generate, but also to look introspectively to ensure that the machinery inside Brit Re is actually fit for purpose.” That machinery includes core operational tools, from data ingestion to modelling. Here, Brit Re is building out its capabilities to match the operational demands of the reinsurance business in Bermuda, making sure that they have the fleet of foot responsiveness and are shaping a business that can deliver a quick answer for brokers. And, for the coming months, the roadmap is threefold: deepen relationships with existing high-quality insurers, expand the submission pipeline and extend geographically. “We’d like to expand our appetites beyond that ‘business-as-usual’ that we’ve engaged a bit more internationally in the last year. [We’ll] try and find some opportunities outside the US market for both property cat and casualty.” Stephenson went on to say: “The mood music in the industry post-Monte Carlo suggests that it’s going to become increasingly competitive. I think that means that we have to be very thoughtful about how and where we deploy our capacity.” When asked what distinguishes Brit Re in a crowded space, Stephenson returned to the fundamentals. “We’ve spent a great deal of time with brokers and ceding companies to try to understand exactly what that looks like from their perspective. Ultimately, our goal is to be considered a stable capital partner to our clients and our brokers. We want to be in it for the long term.” This, he told IB, aligns closely with Fairfax’s DNA – what he calls patient but appropriately demanding capital. ‘We’re here and we’re open for business’“As a broker, I established my own points of view about what I thought value looked like in the reinsurance community – clarity of appetite. We’ve been quite explicit in communicating that with the broker community and with our clients and prospective clients. What are we capable of looking at? How do we view risk? What is the capacity that we can put down on a slip?” However, Stephenson doesn’t shy away from pointing out industry inefficiencies. The main aspect he disliked as a broker was the slow rolling of noes. “When you’re chatting with a market that’s ultimately not going to be able to support you, I’d rather hear that upfront. Our approach to the market should be similar. We’re going to be fairly explicit about our appetites – what goes along hand in hand with that is a speed of response and service. “The same philosophy applies to all of the post-transaction aspects of our business from papering the transactions to accounting for them, and obviously the claims that will be associated with the business in the future.” Stephenson’s confidence in the Bermuda platform is deeply personal. As he told IB, he took his first business trip to Bermuda in 1995 or 1996, trying to source short-tail capacity from the marketplace for non-property cat business, and it was an uphill battle. Today, it’s transformed. “We’re very pleased with our first year after the launch,” added Stephenson. “We’re actively demonstrating our presence in Bermuda, not only through our underwriting but also through support of the industry. We’ve actually invested in a little advertising in L.F. Wade Airport here. It’s a gentle reminder to the community at large, and to lots of people travelling through Bermuda, that we’re here and we’re open for business.”

Source: Brit Re

Jonathan Stephenson, Head of office at Brit Re

Prior to joining Brit, Jonathan was a managing director at Guy Carpenter, based in Toronto. During his more than 30-year career in reinsurance, Jonathan has been Pacific Region CEO for Guy Carpenter and an executive vice president at Aon. Jonathan leads Brit in Bermuda, helping to drive its planned expansion of Brit Re across property, casualty and specialty reinsurance. As a full-service reinsurance platform, Brit Re will represent an important new growth pillar for the group and its global reinsurance capabilities and will complement Brit’s existing successful property reinsurance offering, which writes on behalf of Lloyd’s Syndicate 2987.

Source: Brit Re

Brit Re: a glimpse inside the firm

Brit reinsurance business represents 24% of Brit Group premiums. Both our property and casualty treaty teams have delivered strong and consistent performance over a number of years, driven by our talented and experienced team of lead underwriters who offer our core client base meaningful long-term support. We continue to be a “go-to” market for treaty business in Lloyd’s. Our casualty and property treaty offerings in the US and Bermuda broaden our distribution capability and relationships while leveraging the strength of the reinsurance product in London.